KR840005079A - Method for preparing carboxyalkyl dipeptide - Google Patents

Method for preparing carboxyalkyl dipeptide Download PDF

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KR840005079A
KR840005079A KR1019830002507A KR830002507A KR840005079A KR 840005079 A KR840005079 A KR 840005079A KR 1019830002507 A KR1019830002507 A KR 1019830002507A KR 830002507 A KR830002507 A KR 830002507A KR 840005079 A KR840005079 A KR 840005079A
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aryl
lower alkyl
formula
alanine
dipeptide
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KR910001720B1 (en
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제이.그린리 윌리암
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제임스 에프. 노프톤
머크 앤드 캄파니, 인포코레이티드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06052—Val-amino acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06043—Leu-amino acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
    • Y10S530/80—Antihypertensive peptides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

내용 없음No content

Description

카복시아킬 디펩타이드의 제조방법Method for preparing carboxycyal dipeptide

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (10)

일반식 Ⅱ의 화합물을 디펩타이드와 반응시키면, 디카복시 디펩타이드를 수득하고, 이카복시 디펩타이드를 산성매진; 알코올 용매중에서 수소화하고 동시에 에스테로화하면 부분입체이성체의 혼합물로서 디카보알콕시 디펩타이드를 수득하고, 이 부분입체이성체의 혼합물을 분리하여 일반식 I 의 화합물을 생산함을 포함하는 일반식 I 의 카복시알킬디펩타이드 또는 약학적으로 허용될 수 있는 이의 염의 제조방법.Reacting the compound of Formula II with a dipeptide yields a dicarboxy dipeptide, acidic the icarboxy dipeptide; Hydrogenation in alcoholic solvents and simultaneous esterification yields dicarboalkoxy dipeptides as mixtures of diastereomers and carboxylates of formula I comprising separating the mixture of diastereomers to produce compounds of formula I Method for preparing alkyldipeptides or pharmaceutically acceptable salts thereof. 상기식에서, R 은 아릴, 저급알킬, 저급알콕시 또는 할로등의 치환기로 치환된 아릴, 임의 O 또는 N 원자를 함유할 수 있는 헤테로아릴, 할로, 디할로, 저금알킬, 하이드록시, 저저급알콕시, 아실아미노, 할로저급알킬 등의 치환기가 아릴 및 헤테로아릴 그룹에 치환된 헤테로아릴이고, R1은 탄소수 1내지 4의 저급알킬이고, X는 알라닌, 글리신, 이소루이신, 루이신, 리진, 페닐알라닌, 발린등이고, Y는 알라닌, 글리신, 이소루이신, 루이신, 리진, 페닐알라닌, 프롤린, 발린등이다.Wherein R is aryl substituted with a substituent such as aryl, lower alkyl, lower alkoxy or halo, heteroaryl which may contain any O or N atom, halo, dihalo, lower alkyl, hydroxy, lower alkoxy, Substituents such as acylamino and halo lower alkyl are heteroaryl substituted with aryl and heteroaryl groups, R 1 is lower alkyl having 1 to 4 carbon atoms, X is alanine, glycine, isoleucine, leucine, lysine, phenylalanine And valine, and Y is alanine, glycine, isoleucine, leucine, lysine, phenylalanine, proline, valine and the like. 제1항에서, R은 아릴 또는 치환된 아릴이고, R1, X와 Y는 제1항과 같은 일반식 I 화합물의제조방법.2. The method of claim 1 , wherein R is aryl or substituted aryl, and R 1 , X and Y are the same as those of claim 1. 제1항에서,R은 페닐이고, R1은 에틸이고, X와 Y는 제1항과 같은 일반식 I 화합물의제조방법.The method of claim 1 , wherein R is phenyl, R 1 is ethyl, and X and Y are general formula I compounds as in claim 1. 제1항에서, R은 페닐이고, R1은 에틸이고, X는 알라닌이고, Y는 프롤린인, 일반식 I 화합물의 제조방법.The method of claim 1 , wherein R is phenyl, R 1 is ethyl, X is alanine, and Y is proline. 제1항에세 디카복시디펩타이트를 pd/c촉매 존재하 처리하는 방법.The method of claim 1, wherein the dicarboxydipeptite is treated in the presence of a pd / c catalyst. 제1항에서, 부분입체 이성체의 혼합물을 이온교환 크로마토그라피 및 중압액체 크로마토그라피로 분리하는 방법.The method of claim 1, wherein the mixture of diastereoisomers is separated by ion exchange chromatography and medium pressure liquid chromatography. 일반식 Ⅱ의 화합물을 디펩타이드 벤질에스테르 하이드로 클로라이드와 반응시키면 보호된 디펩타이드 에스테르를 수득하고, 이 에스테르를 촉매적으로 처리하면, 중첩보호된 디펩타이드 에스테르를 수득하고, 중첩보호된 디펩타이드 에스테르를 아세토니트릴과 말레산으로 처리하면, S,S,S―입체이성체 말레이트 염으로서 일반식 I 화합물을 수득하는 것을 포함하는 일반식 I 의 카복시알킬 디펩타이드와 약학적으로 허용될 수 있는 이의 염의 제조방법.Reaction of the compound of formula II with dipeptide benzyl ester hydrochloride yields a protected dipeptide ester, and catalytic treatment of this ester yields a superprotected dipeptide ester and Preparation of carboxyalkyl dipeptides of Formula I and pharmaceutically acceptable salts thereof comprising treating with acetonitrile and maleic acid yielding compounds of Formula I as S, S, S-stereoisomer maleate salts Way. I I 상기식에서, R은 아릴, 저금알킬, 저급알콕시 또는 할로등의 치환기로 치환된 아릴, 임의 O 또는 N 원자를 함유할 수 있는 헤테로아릴, 할로, 디할로, 저급알킬, 하이드록시, 저급알록시, 아실아미노, 할로저급알킬 등의 치환기가 아릴 및 헤테로아릴 그룹에 치환된 헤테로아릴이고, R1은 탄소수 1내지 4의 저급알킬이고, X는 알라닌, 글리신, 이소루이신, 루이신, 리진, 페닐알라닌, 발린등이고, Y는 알라닌, 글리신, 이소루이신, 루이신, 리진, 페닐알라닌, 프롤린발린등이다.Wherein R is aryl substituted with a substituent such as aryl, lower alkyl, lower alkoxy or halo, heteroaryl which may contain any O or N atom, halo, dihalo, lower alkyl, hydroxy, lower hydroxy, Substituents such as acylamino and halo lower alkyl are heteroaryl substituted with aryl and heteroaryl groups, R 1 is lower alkyl having 1 to 4 carbon atoms, X is alanine, glycine, isoleucine, leucine, lysine, phenylalanine And valine, and Y is alanine, glycine, isoleucine, leucine, lysine, phenylalanine, prolinevaline and the like. 제7항에서, R은 아릴 또는 치환된 아릴이고 R1,X와 Y는 제1항과 같은 일반식 I 화합물의 제조방법.8. A process according to claim 7, wherein R is aryl or substituted aryl and R 1 , X and Y are the same as defined in claim 1. 제7항에서, R은 페닐이고, R1은 에틸이고, X와 Y는 제1항과 같은 일반식 I 화합물의 제조방법.8. A process according to claim 7, wherein R is phenyl, R 1 is ethyl and X and Y are general formula I compounds as in claim 1. 제7항에서, R은 페닐이고, R1은 에틸이고, X는 알라닌이고, Y는 프롤린인, 일반식 I 화합물의 제조방법.8. A process according to claim 7, wherein R is phenyl, R 1 is ethyl, X is alanine and Y is proline. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019830002507A 1982-06-07 1983-06-04 Process for preparation of carboxyalkyl dipeptide KR910001720B1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US38574582A 1982-06-07 1982-06-07
JP385745 1982-06-07
JP462727 1983-01-31
US06/462,727 US4442030A (en) 1982-06-07 1983-01-31 Process for preparing carboxyalkyl dipeptides
US385745 1989-07-27

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KR910001720B1 KR910001720B1 (en) 1991-03-22

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US (1) US4442030A (en)
KR (1) KR910001720B1 (en)
AT (1) AT393508B (en)
ES (2) ES522753A0 (en)
GR (1) GR78282B (en)
NO (1) NO166231C (en)
PT (2) PT76790B (en)

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US4746676A (en) * 1984-09-12 1988-05-24 Rorer Pharmaceutical Corporation Carboxyalkyl dipeptide compounds
AR021803A1 (en) * 1998-09-23 2002-08-07 Merck & Co Inc PERFECTED STEREOSELECTIVE PROCESS FOR ENALAPRIL.

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IL58849A (en) * 1978-12-11 1983-03-31 Merck & Co Inc Carboxyalkyl dipeptides and derivatives thereof,their preparation and pharmaceutical compositions containing them

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ES535853A0 (en) 1985-07-01
PT76790B (en) 1986-04-09
NO166231B (en) 1991-03-11
US4442030A (en) 1984-04-10
AT393508B (en) 1991-11-11
ES8506264A1 (en) 1985-07-01
ATA201283A (en) 1991-04-15
NO832036L (en) 1983-12-08
NO166231C (en) 1991-06-19
GR78282B (en) 1984-09-26
ES8502082A1 (en) 1984-12-16
PT76790B1 (en) 1996-09-30
KR910001720B1 (en) 1991-03-22
PT76790A (en) 1983-07-01
ES522753A0 (en) 1984-12-16

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